Anthraquinone dyestuffs



ANTHRAQUINONE DYESTUFFS No Drawing. Filed Dec. 30, 1952, Ser. No. 328,816

3 Claims. (Cl. 260-380) The present inventionrelates to the production of dyestulfs of the anthraquinone series and more particularly to unsulfonated compounds having the following general formula: 1

ouitoclnnlon 7 wherein one R stands for N and the other R stands for OH, X is selected from the group consisting of hydrogen, halogen and lower alkyl, Y is selected from the group consisting :of hydrogen and OH OC H;),',OH, and n has a value of 1 to 3. V

The need for dysetuffs in the violet blue and green range which are fast to light and to acid gas fumes when applied to cellulose acetate rayon has beenlon-g recognized. In the compounds of the. formula described above, we have discovered a series of dyestuffs which combine the desirable properties of good substantivity and good light fastness, wash'fastness and acid gas fastness. Such dyestuffs are also applicable to materials having a basis of nylon, Dacron,Orlon, Dynel, Acrilan and other polymeric substances.

The dyestuffs of this invention may be prepared readily bYCOndenSing a 1.,8-dihydroxy, 4,5dinitro or .LS-dihy- ,dr y-lij-dinitn) anthraquinone with a properly subt tl t d aminobenzene. ,Catalystsjand acid binding agents may bewemployed if desired, and thenreaction ,may be carried out preferably in the absence of water and in an inert organc diluent.

'The above-mentioned properly substituted aminobenzenes, namely, those of the formula IJHK nHOnOH wherein X, Y and n have the values stated hereinbefore, and their method of production, are disclosed and claimed in the copending application of Saul R. Buc and David I. Randall, Serial No; 128,919 filed November 22, 1949, now abandoned.

It will be readily understood that the compounds of the instant invention may be substituted in the benzene nucleus of the 4-benzeneamino substituent and in the 2,3,6 and 7 positions of the tanthraquinone nucleus by inert substituents' which do not detract from the properties desired in the final dyestufl. In the formula, X may be hydro-gen, methyl, ethyl, propyl, Cl, Br, and the like, but preferably hydrogen, or methyl, and w preferably has a value of 1.

The following examples serve to illustrate the inven- United States Patent ffice .tion but they are not intended to limit it thereto. Parts In a suitable vessel equipped with a stirrer, a, heater, a thermometer and a condenser were placed 165 parts 4,5- dinitrochrysazine, 281 parts- 2,2.-(4-amino-2,6-tolylenedimethoxy)diethanol and 1,750 parts nitrohenzene. The reaction mixture was maintained at 150 C. for 7 /2 hours duringwhich time the mixture was stirred. It was allowed to cool and water was added. Steam distillation was then conducted until all of the solvent had been driven over. The residue was isolated by decantation and stirred with 1000 parts warm methanol. The part which was undissolved in the methanol was isolated by filtration and the process repeated twice more. The final residue after drying weighed 300 parts; 1 It'has the structure:

Hzocnlongon crno cmcmon'.

' tionally good fastness to the action of combustion gas fumes.

Example 2 The process of Example 1 was repeated except that 195 parts Z-m-arninobenzyloxyethanol were used in place of the 281 parts 2,2-(4-amino2,6-tolylenedimethoxy)diethanol. The dysetutf which resulted has the structure:

m d OH c1120 cnlcmon N02 Nil- It gave dyeings of essentially the same fastness properties as those of the dyestutf described in Example 1. It was slightly redder in shade.

Example 3' HO 0 OH $H2OCH2CH2OH I No, 0 NH-O-OH:

Examp le4 The process of Example 1 was repeated except that 234 parts of 2-(Z-m-aminobenzyloxyethoxy)ethanol were used instead of the 281 parts 2,2-(4 amino-2,6tolylenedimethoxy)diethanol. The resulting dyestufi has substan- Patented July 19, 1960* 3 V 4 tially the same properties as those of Example 2, and has Various modifications and variations of this invention the structure: will be obvious to a person skilled in the art and such HO O OH variations and modifications are to be regarded as within I V p 7 the purview of this application and the spirit and scope 6 of the appended claims.

. a We claim: (EHOGHCHBOCHCHOH 1. A compound of the formula I Q n OH NO: 0 NH I I 10 Example 5 Theprocess of Example 1 was repeated except that 'oH, oo,r1. .,oH an equal weight of 4,8-dinitroanthrar-ufin was used in I place of the 4,5-dinitrochrysazine. The product was 0 NH X slightly greener than the product of Example 1 and gave V dyeings of substantially the same fastness properties. CHz(OC:H4)nOH It has the structure:

N 0 or; wherein one R stands for N0 and the other R stands for l 0H, X is selected from the group consisting of hydrogen, halogen and lower alkyl, and n has a value of Ho 3.

2. The compound of the formula CHQOCHZCHflOH p '4 E0 OH H d NH CH:

crnocrncmorr omoomomon Example 6 v I The process of Example2 was repeated except that NO: 0 NH -GH; an equal weight of 4,8-dinitroanthrarufin was used in place of the 4,5-dinitrochrysazine. The product was HIOCHICHlOH slightly greener than the product of Example 2 and had a substantially the same fastness properties. It has the 3. The compound of the formula structure: a5 O O OH 3 0H 2: J; i ,,t

(IDHOCHCHOH V 0 CHnOCHzCHzOliI Example 7 H O CHflOHiOH The process of Example 3 was; repeated except that i an equal weight of 4,8 dinitroanthramfin was used in References Cited 1n the file of this-patent I place of the 4,5-dinitrochrysazine. The properties of UNITED STATES PATENTS the products of the two examples were substantially the v v 1,960,564 Zahn et a1 May 29' 1934 same. The product of this example has the structure. 2,560,887 Randall aL d July 1951 1 OH a r 2,585,681 Randall et a1. Feb. 12, 1952 2,641,602 Straley et al. June 9, 1953 CHgOOH CHgOH 

1. A COMPOUND OF THE FORMULA 